Maui Economic Development Board (MEDB) welcomed marketing strategist Jennifer Apy for two very engaging and insightful presentations on brand growth, innovation, and the evolving role of artificial intelligence in business. Wednesday July 9 was the popular Maui Techohana where 37 small business owners met at MEDB’s Malcolm Center for networking and a presentation that offered a blend of storytelling, strategy, and actionable insights. A further 15 joined via the livestream.
Apy, a Baldwin High School graduate with degrees from Brown University and Stanford, shared her journey from leading marketing initiatives at Fortune 500 companies like Adobe and Mattel to helping small businesses thrive through her work with Chief Outsiders.
Through real-world case studies—like the viral success of ZÜCA bags in the disc golf community—Apy emphasized the importance of emotional connection, customer insight, and iterative testing in successful marketing. She introduced the concept of the “emotional why” as a key to building lasting brand loyalty.
Apy also explored the power of generative AI in marketing, demonstrating how tools like ChatGPT can be used not just for content creation, but for data analysis, customer segmentation, and campaign optimization. She outlined a four-stage AI adoption model and encouraged businesses to move from experimentation to strategic implementation.
Jennifer Apy leads a workshop on Marketing and AI at MEDB’s Malcolm Center
“I thought the presentation was excellent,” said David Yamashiro, Founder of Ululani Shave Ice. “She (Apy) is a well-respected expert in her field. My key take away is that I definitely want to come to the follow-up workshop so that I can see how to best apply AI to benefit our business. There are so many ways that I didn’t even think possible.”
Jennifer returned on Thursday for a hands-on workshop to explore AI tools in depth, with opportunities for one-on-one office hours. Titled Unlock AI for Your Business: Hands-On Workshop for Growth, Sales & Productivity the workshop was tailored towards the 33 attending in-person and 15 livestream with Jen first learning about participant’s experience and what they were hoping to learn.
In addition to ChatGPT, Apy referenced Perplexity, Microsoft’s Copilot, Claude and Google Gemini (to name a few.) Apy gave many different examples of detailed prompts she has used to analyze customer segments, how to hone in to get the results you need, and how to use the results for next steps. Other case-uses included product prototyping and document creation. Apy also gave tips on keeping your data confidential and being aware of AI limitations as well as possibilities.
“MEDB is committed to equipping Maui’s business community with cutting-edge tools and knowledge,” said Annette Lynch, MEDB’s Director of Communications. “We are grateful to experts like Jennifer, with a connection to Maui and so much knowledge and real-world experience, to be able to come and teach our community the tools and resources to help their businesses thrive.”
Apy co-founded and sold an enterprise Saas software company in 2021, and is currently invested in a broad portfolio of startups. After 3 decades of marketing leadership on the continent, Jennifer Apy’s work has brought her home to mentor companies for business accelerators in Hawaii.
Maui Economic Development Board (MEDB) is a 501(c)(3) not-for-profit corporation established in 1982 with a mission to diversify Maui County’s economy, building pathways to innovation, jobs and opportunities for our residents. Through partnerships with the public and private sector, MEDB undertakes projects that assist growth industries with navigating and thriving in our county, educates and trains residents for new careers, and engages our community in forums that determine future economic directions.